Synthesis of mannojirimycin derivatives
US5101027A · kind A · utility
3Cited by
1References
1Claims
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Inventors
Key dates
| Filing date | Dec 17, 1990 |
| Grant date | Mar 31, 1992 |
| Priority date | — |
| Expiry date | Dec 17, 2010 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F7/1804
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
.alpha.-Homojirimycin and 6-dpi-homojirimycin are each synthesized from 2 az ido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-la ctone in which the side chain acetonide is hydrolyzed to give the corresponding diol which is then protected with a silyl protecting agent to form a silyl ether. The latter compound is used as a divergent intermediate in which the piperidine ring is formed by joining the nitrogen function at C-2 to C-6 (A) with inversion of configuration at C-6 to form 6-epi-homomannojirimycin or (B) with retension of configuration at C-6 to form .alpha.-homomannojirimycin.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.